IMPPAT Phytochemical information: 
Triglochinin
Triglochinin
Summary

SMILES: OC[C@H]1O[C@@H](O/C(=C(\CC(=O)O)/C=C\C(=O)O)/C#N)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C14H17NO10/c15-4-7(6(3-10(19)20)1-2-9(17)18)24-14-13(23)12(22)11(21)8(5-16)25-14/h1-2,8,11-14,16,21-23H,3,5H2,(H,17,18)(H,19,20)/b2-1-,7-6-/t8-,11-,12+,13-,14-/m1/s1
InChIKey: LABCALMTQNDOAI-PKNBYVPASA-N
DeepSMILES: OC[C@H]O[C@@H]O/C=C\CC=O)O)))/C=C\C=O)O)))))/C#N))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1CCOCC1
Scaffold Graph/Node level: C1CCOCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CO; CC(/C=C\C(=O)O)=C(/C#N)O[C@@H](C)OC; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
triglochinin (cyanogenetic glucoside), triglochinin, triglochinin (o-[β-d-glucopyranosyl]-1-cyano-1-hydroxy-2-methylcarboxy-4-carboxy-δ-1,2(e)-δ-3, (z)-butadiene), Triglochinin
External chemical identifiers:
CID:CID_5281124; ChEBI:CHEBI:9717; ZINC:ZINC000004097538
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Triglochinin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 359.29
Log P RDKit -2.3
Topological polar surface area (Å2) RDKit 197.77
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1
Triglochinin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.12
Triglochinin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.53
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No